Alkylsubstituted thienothiophene semiconducting materials: Structure-property relationships

Journal of the American Chemical Society

Volumn 131, Issue 33, 2009, Pages 11930-11938

  He, Mingqian ^a   Li, Jianfeng ^a   Sorensen, Michael L ^a   Zhang, Feixia ^a   Hancock, Robert R ^a   Hon, Hang Fong ^b   Pozdin, Vladimir A ^b   Smilgies, Detlef M ^c   Malliaras, George G ^c  

^a SP FR 6 ^*  (United States)

^b Cornell University   (United States)

^c Department of Obstetrics Gynecology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AFM; ALKYL SIDE CHAINS; CRYSTALLINE STRUCTURE; EXTENDED CONJUGATION; FIELD-EFFECT TRANSISTORS; FUSED THIOPHENE; ODD NUMBERS; ORDER OF MAGNITUDE; OXIDATIVE STABILITY; POLYMER BACKBONES; POLYMER ELECTRONICS; PROPER DESIGN; SEMICONDUCTING MATERIALS; SIDE CHAINS; STRUCTURE PROPERTY; STRUCTURE PROPERTY RELATIONSHIPS; THIENOTHIOPHENES; THIOPHENE RING; X- RAY DIFFRACTION;

CONJUGATED POLYMERS; ELECTRONIC PROPERTIES; IONIZATION POTENTIAL; ORGANIC POLYMERS; POLYMERS; THIOPHENE;

STRUCTURAL PROPERTIES;

ALKYL GROUP; POLY (2,5 BIS(THIOPHENE 2 YL) (3,5 DIDECANYLTRITHIENOACENE); POLY(2,5 BIS(THIOPHENE 2 YL) (3,6 DIDECANYLPENTATHIENOACENE); POLY(2,5 BIS(THIOPHENE-2 YL) (3,7 DIDECANYLTETRATHIENOACENE); POLYMER; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLIC POTENTIOMETRY; IONIZATION; OXIDATION; SEMICONDUCTOR; SUBSTITUTION REACTION; SYNTHESIS; ULTRAVIOLET RADIATION; X RAY DIFFRACTION;

ALKANES; CHROMATOGRAPHY, GEL; ELECTROCHEMISTRY; POLYMERS; SEMICONDUCTORS; SPECTROPHOTOMETRY, ULTRAVIOLET; STRUCTURE-ACTIVITY RELATIONSHIP; TEMPERATURE; THIOPHENES; TRANSISTORS, ELECTRONIC; X-RAY DIFFRACTION;

EID: 69049107498     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja903895s     Document Type: Article

References (45)

1. Allard, S.; Forster, M.; Souharce, B.; Thiem, H.; Scherf, U. Angew. Chem., Int. Ed. 2008, 47, 4070.
2. Sirringhaus, H.; Brown, P. J.; Friend, R. H.; Nielsen, M. M.; Bechgaard, K.; Langeveld-Voss, B. M. W.; Spiering, A. J. H.; Janssen, R. A. J.; Meijer, E. W.; Herwig, P.; de Leeuw, D. M. Nature 1999, 401, 685.
3. Anthony, J. Chem. Rev. 2006, 106, 5028.
4. Liu, S.; Wang, W. M.; Briseno, A. L.; Mannsfeld, S. C. B.; Bao, Z. Adv. Mater. 2009, 21, 1217.
5. (a) Podzorov, V.; Menard, E.; Borissov, A.; Kiryukhin, V.; Rogers, J. A.; Gershenson, M. E. Phys. Rev. Lett. 2004, 93, 086602.
6. (b) Sundar, V. C.; Zaumseil, J.; Podzorov, V.; Menard, E.; Willett, R. L.; Someya, T.; Gershenson, M. E.; Rogers, J. A. Science 2004, 303, 1644.
7. Yamagishi, M.; Takeya, J.; Tominari, Y.; Nakazawa, Y.; Kuroda, T.; Ikehata, S.; Uno, M.; Nishikawa, T.; Kawase, T. Appl. Phys. Lett. 2007, 90, 182117.
8. He, M.; Zhang, F. J. Org. Chem. 2007, 72, 442.
9. Zhang, X.; Cote, A. P.; Matzger, A. J. Am. Chem. Soc. 2005, 127, 10502.
10. Mazaki, Y.; Kobayashi, K. Tetrahedron Lett. 1989, 25, 3315.
11. McCulloch, I.; Heeney, M.; Bailey, C.; Genevicius, K.; Macdonald, I.; Shkunov, M.; Sparrowe, D.; Tierney, S.; Wagner, R.; Zhang, W.; Chabinyc, M. L.; Kline, R. J.; McGehee, M. D.; Toney, M. F. Nat. Mater. 2006, 5, 328.
12. McCulloch, I.; et al. Adv. Mater. 2009, 21, 1091.
13. Hamadani, B. H.; Gundlach, D. J.; McCulloch, I.; Heeney, M. Appl. Phys. Lett. 2007, 91, 243512.
14. Chabinyc, M. L.; Toney, M. F.; Kline, R. S.; McCulloch, I.; Heeney, M. J. Am. Chem. Soc. 2007, 129, 3226.
15. Umeda, T.; Tokito, S.; Kumaki, D. J. Appl. Phys. 2007, 101, 054517.
16. (a) Kline, R. J.; DeLongchamp, D. M.; Fischer, D. A.; Lin, E. K.; Heeney, M.; McCulloch, I.; Toney, M. F. Appl. Phys. Lett. 2007, 90, 062117.
17. (b) Lucas, L. A.; DeLongchamp, D. M.; Vogel, B. M.; Lin, E. K.; McCulloch, I.; Heeney, M.; Jabbour, G. E. Appl. Phys. Lett. 2007, 90, 012112.
18. Osaka, I.; Zhang, R.; Sauvé, G.; Smilgies, D.-M.; Kowalewski, T.; McCullough, R. D. J. Am. Chem. Soc. 2009, 131, 2521.
19. Osaka, I.; Sauvé, G.; Zhang, R.; Kowalewski, T.; McCullough, R. D. Adv. Mater. 2007, 19, 4160.
20. Kim, D. H.; Lee, B.-L.; Moon, H.; Kang, H. M.; Jeong, E. J.; Park, J.-I.; Han, K.-M.; Lee, S.; Yoo, B. W.; Koo, B. W.; Kim, J. Y.; Lee, W. H.; Cho, K.; Becerril, H. A.; Bao, Z. J. Am. Chem. Soc. 2009, 131, 6124.
21. Fong, H. H.; Pozdin, V. A.; Amassian, A.; Malliaras, G. G.; Smilgies, D.-M.; He, M.; Gasper, S.; Zhang, F.; Sorensen, M. J. Am. Chem. Soc. 2008, 130, 13202.
22. (a) Yan, He.; Chen, Z.; Zheng, Y.; Newman, C.; Quinn, J. R.; Dötz, F.; Kastler, M.; Facchetti, A. Nature 2009, 457, 679.
23. (b) Chen, Z.; Zheng, Y.; Yan, H.; Facchetti, A. J. Am. Chem. Soc. 2009, 131, 8.
24. (a) Hakan, U.; Chad, R.; Wang, Z.; Huang, H.; Deliomeroglu, Murat., K.; Zhukhovitskiy, A.; Facchetti, A.; Marks, T. J. J. Am. Chem. Soc. 2009, 131, 5586.
25. (b) Hakan, U.; Facchetti, A.; Marks, T. J. J. Am. Chem. Soc. 2008, 130, 8580.
26. (a) Loo, Y.-L.; McCulloch, I. MRS Bull. 2008, 33, 653.
27. (b) Organic Field-Effect Transistors, 1st ed.; Bao, Z., Locklin, J., Eds.; CRC Press: Boca Raton, FL, 2007.
28. (c) Organic Electronics: Materials, Manufacturing and Applications; Klauk, H., Ed.; Wiley-VCH: Weinheim, Germany, 2006.
29. (d) Semiconducting Polymers: Chemistry, Physics and Engineering; Hadziioannou, G., Malliaras, G. G., Eds.; Wiley-VCH: Weinheim, Germany, 2007.
30. (e) Sirringhaus, H.; Tessler, N.; Friend, R. H. Science 1998, 280, 1741-1744.
31. (f) Huitena, H. E. A.; Gelinck, G. H.; van der Putter, J. B. P. H.; Kuijk, K. E.; Hart, C. M.; Cantatore, E.; Herwig, P. T.; van Breemen, A. J. J. M.; de Leeuw, D. M. Nature 2001, 414, 599.
32. (g) Bao, Z. Adv. Mater. 2000, 12, 227-230.
33. (h) Li, Y. N.; Wu, Y. L.; Ong, B. S. Macromolecules 2006, 39, 6521.
34. Kline, R. J.; DeLongchamp, D. M.; Fischer, D. A.; Lin, E. K.; Richter, L. J.; Chabinyc, M. L.; Toney, M. F.; Heeney, M.; McCulloch, I. Macromolecules 2007, 40, 7960.
35. Agrawal, A. K.; Jenekhe, S. A. Chem. Mater. 1996, 8, 579.
36. WAXS / GIWAXS @ D1: Conversions: http://staff.chess.cornell.edu/ ∼smilgies/D-lineNotes/GISAXS-at-D-line/GIWAXS@D1-Conversions. html.
37. (a) Busch; et al. J. Appl. Crystallogr. 2006, 39, 433.
38. (b) Breiby; et al. J. Appl. Crystallogr. 2008, 41, 262.
39. Azumi, R.; Mena-Osteritz, E.; Boese, R.; Benet-Buchholz, J.; Baeuerle, P. J. Mater. Chem. 2006, 16, 728.
40. DeLongchamp, D. M.; Kline, R. J.; Lin, E. K.; Fischer, D. A.; Richter, L. J.; Lucas, L. A.; Heeney, M.; McCulloch, I.; Northrup, J. E. Adv. Mater. 2007, 19, 833.
41. Northrup, J. E. Phys. Rev. B 2007, 76, 245202.
42. Ong, B. S.; Wu, Y.; Liu, P.; Gardner, S. J. Am. Chem. Soc. 2004, 126, 3378.
43. Zen, A.; Pflaum, J.; Hirschmann, S.; Zhuang, W.; Jaiser, F.; Asawapirom, U.; Rabe, J. P.; Scherf, U.; Neher, D. Adv. Funct. Mater. 2004, 14, 757.
44. Kline, R. J.; McGehee, M. D.; Kadnikova, E. N.; Liu, J.; Fréchet, J. M. J. Adv. Mater. 2003, 15, 1519.
45. Yang, H.; Shin, T. J.; Yang, L.; Cho, K.; Ryu, C. Y.; Bao, Z. Adv. Funct. Mater. 2005, 15, 671.